Réaction #7830

Équation de réaction

[4-(1,3-Benzoxazol-2-yl)-2-methoxyphenyl]acetonitrile

Sodium bis(trimethylsilyl)amide

1,4-dibromobutane

→

1-[4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]cyclopentanecarbonitrile

Solvants

THF

Conditions de réaction

Traitement

1. 1
   ConcentrationAfter concentrating
2. 2
   Autrereaction mixture in vacuo
3. 3
   Autrethe resulting pink oil was purified by flash chromatography
4. 4
   Lavagea gradient elution of 1:9 EtOAc

Mode opératoire

[4-(1,3-Benzoxazol-2-yl)-2-methoxyphenyl]acetonitrile (130 mg, 0.49 mmol) in THF (5.0 mL) was cooled to −78° C. under argon atmosphere. Sodium bis(trimethylsilyl)amide (1.8 mL, 1.08 mmol) was added slowly and after fifteen minutes, added 1,4-dibromobutane (0.07 mL, 0.59 mmol) to dark brown reaction mixture. Let mixture warm to rt overnight. After concentrating reaction mixture in vacuo, the resulting pink oil was purified by flash chromatography, using a gradient elution of 1:9 EtOAc:hexanes to 1:4 EtOAc:hexanes. This afforded the desired compound, 1-[4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]cyclopentanecarbonitrile, as a yellow solid. 1H NMR(CDCl3, 300 MHz) δ 7.86–7.26 (m, 7H), 4.07 (s, 3H), 2.59–1.91 (m, 8H). MS (ESI) 319.1 (M+H)+.

Source